Ammonia → 3-(6-Fluorooxazolo[4,5-b]pyridin-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

HRID 908417Notes

Reaction equation

HRID 908417 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:26]1[O:27][C:28]2[C:29]([N:35]=1)=[N:30][CH:31]=[C:32]([F:34])[CH:33]=2.Cl.N>ClCCl>[F:34][C:32]1[CH:33]=[C:28]2[O:27][C:26]([C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]4[CH:9]=[N:10][N:11]([CH:13]5[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]5)[CH:12]=4)[CH:4]=3)=[N:35][C:29]2=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 67389039Tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 576871183-(6-Fluorooxazolo[4,5-b]pyridin-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amineYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (190 mg) and hydrogen chloride (4M solution in dioxane) (4.95 ml) in dichloromethane (2 ml) was stirred at room temperature for 2 hours. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford a solid, which was taken up into 5% methanolic ammonia (7 N) in dichloromethane (20 ml) and stirred for 10 minutes. The suspension was filtered, concentrated and the resulting solid was stirred in acetonitrile (2 ml) for 2 hours at room temperature. It was collected by filtration and dried to a constant weight to afford 3-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (110 mg). NMR Spectrum: (CDCl3) 1.88-2.03 (m, 2H), 2.18-2.27 (m, 2H), 2.76-2.84 (m, 2H), 3.23-3.33 (m, 2H), 4.23-4.33 (m, 1H), 6.86 (bs, 2H), 7.67 (dd, 1H), 7.70 (s, 1H), 7.78 (s, 1H), 8.36 (d, 1H), 8.44 (d, 1H), 8.48 (dd, 1H); Mass spectrum: M+H+ 380.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. customdried
  4. customto afford a solid, which
  5. stirringstirred for 10 minutes
  6. filtrationThe suspension was filtered
  7. concentrationconcentrated
  8. stirringthe resulting solid was stirred in acetonitrile (2 ml) for 2 hours at room temperature
  9. filtrationIt was collected by filtration
  10. customdried to a constant weight

Sources & evidence

ORD record
ord-008b377f7a9747b29e9fc62a7f65a3c0
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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